This Professional Risk-Taker Explains Why Exceptional Leaders Aren’t Always Confident with Their Decisions

In the early aughts, Annie Duke was an unbeatable poker player. At the very first World Series of Poker Tournament of Champions in 2004, she brought home the trophy and a $2 million pot. Later, in 2012, she turned her gambling wins into a speaking business, offering classes to Wall Street traders on risky decision-making and what they could learn from her card-playing successes and mistakes. Once that business became self-sustaining, she folded her cards and largely retired from the game to focus on education, her real passion. Drawing on what she’d learned from volunteering for an after-school program in Northern California and the latest research in behavioral economics, she founded How I Decide, a nonprofit that focuses on developing students’ critical thinking and socio-emotional skills. NationSwell spoke with Duke by phone about the topic she knows best: decision-making, its emotions, risks and rewards.
What’s the best advice you have ever been given on leadership?
People believe that to be a good leader, you have to be incredibly confident. They tend to equate confidence with this idea that you’re 100 percent sure about your decisions and that it’s an unwillingness to admit failure. In order to really effectively lead, you have to allow people to understand that confidence is not that. Admitting when you’ve made a mistake or letting people know that you’re not 100 percent sure of every decision is actually a better way to lead. A lot of people I admire have set a great example by saying, “I just wanted to let you know that I just made this really big mistake, and I thought I’d share it with you because I learned from it.”
What innovations in your field are you most excited about right now?
In the world of behavioral economics, there’s a big push recently towards actually applying the research in the field to improving people’s lives in the real world. You can really see this with [Stanford psychologist] Carol Dweck, who is very vocal in saying that she felt like she was sort of locked in a box doing her research for a long time, and now, she’s actually bringing that work to the populations that really need it. With behavioral economics, there was a long period of time where people were saying, “Oh, isn’t this interesting? People are very irrational.” And now that it’s starting to be a focus on, okay, that’s true, but how can we actually improve people’s lives through understanding what we know and trying to figure out real-world strategies that would improve decision-making?  
What’s on your nightstand?
Right now, a bunch of stuff. I’m reading “Superforecasting: The Art and Science of Prediction” [by Philip E. Tetlock and Dan Gardner] and “The Success Equation: Untangling Skill and Luck in Business, Sports and Investing” by Michael Mauboussin. I just finished “Kluge: the Haphazard Evolution of the Human Mind,” which is by Gary Marcus, and “Rethinking Positive Thinking: Inside the New Science of Motivation” [by Gabriele Oettingen], which is fantastic look at mental contrasting.
What do you wish someone had told you when you started this job?
I wish when I first started out as an adult, I had a broader view of what success looked like. I think that I had a super-narrow view of what it meant to be successful, and I wish that there was a more complete view of success, so it also included emotional success: what it means to really be happy or feel fulfilled. I think that there’s a big push right now around mindfulness, which is really wonderful, because I think that it does treat the person as a whole. When I was growing up, success meant you went to this school and you had this kind of job. I think that when I was younger, I was sort of judgmental about that. Like when I met someone, one of the first questions I asked was, “What school did you got to?” As if that matters. I look at people who didn’t take that particular path, and many of them are incredibly successful individuals. But also I think that taught me to be incredibly judgmental of myself, when I felt like I wasn’t being successful or following whatever path I thought I wanted.

Annie Duke gives a talk on Decision Science at World Café Live in Philadelphia.

What’s your proudest accomplishment?
My children. I don’t think that there’s a close second to that.
What inspires you?
As far as poker is concerned, the inspiration was definitely my brother. He was already doing it, and he’s largely responsible for the success that I had, because without his mentorship, I don’t think that it would have happened. Going into the more academic side of things and decision-making, my children really inspired me to work in that [field]. Another person that inspired me is my paternal grandfather, who emigrated from Eastern Europe [and only] graduated from sixth grade, and I went to two Ivy League schools — the journey you can take from getting here not even speaking English to just two generations later. If you get somebody an education, it really removes limitations from their life. I appreciate the arc that happened in my family and how quickly that changed occurred through education.
How do you try to inspire others?
I don’t think about that. I try to focus on doing the stuff that I do, which is what really brings me a lot of happiness. And if someone is inspired by that, that’s great. Obviously, when I’m going and giving speeches, I’m hoping to inspire people to make changes in the way they think. The stuff that we do with kids is to inspire them to continue their education and become better thinkers and all of those things. But me personally, I think if I were really focused on that, I wouldn’t be able to do what I do very well. Because you have to live within yourself and the moment to be effective.
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This interview has been edited and condensed.